The Saga of a (nearly) Decade-old Windows Installation

Windows 7 was something else. Before it we had Vista, an OS with such a bad reputation no amount of fixing could bring it back into favor with the public (or more importantly, the angry mobs that form large swaths of the internet). Vista’s PR problem caused users to double-down even harder on XP, and created a frightening uncertainty surrounding the Windows 7 launch. By this time, most users had spent the better part of 8 years running XP, and had gotten comfortable with it, like an old and worn blanket you just aren’t willing to give up.

But this is where our tale begins. In 2009, Windows 7 hits the market and much to many people’s surprise, isn’t a repeat of the dumpster fire that was Windows Vista. It still didn’t include the fabled longhorn file system (WinFS) first promised by Vista, and by and large people couldn’t understand what made it worth upgrading over XP. But it wasn’t a problem child, so when it was delivered on your new desktop from an OEM or it came time to download an OS for your reformatting ritual that weekend, Win 7 seemed like a safe enough bet. So it was reluctantly but steadily adopted by PC users, eventually including even myself.

Now, something to understand about me. While I am certainly a modern technologist and IT professional, I am often stubborn in my willingness to give up the thing that’s already working for me, and operating systems are as about extreme an example of this behavior as I can think of.
Long after everyone else was using XP, I was still rocking my Win2000, firmly convinced that they would only take it from me by way of my cold, lifeless corpse. I was a die-hard Win2k user, and in my view, XP just had a dumb, fruity, and wholly unnecessary coat of paint on it that wasn’t angsty enough for teenage Tephlon. So I shunned it for years longer than I should have.
Then one day, when it came time to reformat and reinstall (as you were want to do back then, because something broke or you were convinced your quake 3 performance was suffering from a fucked OS install), I decided it was time to give XP the ol’ college try. Sure enough, after enabling the classic theme (fuck that “modern theme” trash!), it turns out this OS is pretty good! Maybe it’s not just Win2k in whore makeup. Hey, this is actually really nice! USB drivers builtin?! Faster boot?! Why was I sticking with 2k? Oh, Yeah. I can’t remember either.

And so it goes for Teph. Every new OS, I play the role of a grumpy old man with kids on my front lawn, pining over the way things used to be, clinging to my dusty old OS far longer than is sensible.

But eventually Win 7 is adopted and I find myself in the strangest of places… my machine is stable! It runs well! Maybe I don’t need to reformat right now! Is this even possible?
Years pass. Service pack 1 is released. Still stable. No BSOD or driver issues that require a reformat. I get comfortable. I’ve tweaked this install for years! Things are just how I like them. Life is good.

Then, Windows 8 is released. There is an outcry from people regarding the fullscreen start menu. “HOW DARE THEY?!”, they exclaim.
But I’m trying to turn a new leaf. “I can’t run Win 7 forever!”, I thought.
I’m presented with an opportunity to purchase a cheap copy of Win8 Pro from the MS company store. I take it. I own Windows 8. But now, what to do? Dare I try this long-dreaded feature called “the upgrade”? I’m sooo comfortable in my Win7 install. I don’t want to start over!10-featured

Screw it. I take the leap! I install Windows 8 as an upgrade over Windows 7.
“This won’t end well”, I thought. “It can’t! I’ll just end up having to reinstall anyway. This is a waste of time!”

But then the craziest thing happened.

Nothing broke. Nothing was noticeably slower or worse post upgrade. No compatibility problems. Did I really just successfully do a Windows upgrade with no adverse side effects?
If this isn’t a phenomenon you are familiar with, lets just say that the long and short of it is that doing an in-place upgrade of a Windows OS didn’t have a great reputation. It had such a bad reputation, in fact, that it just became an automatic fact of life and best practice. You didn’t really question it. An upgrade WILL shit out on you. So don’t even try one.
That, frankly, made the next part even weirder.

Because it kept going. It kept working. No eventual build-up of temp files, orphaned registry entries, drivers and other OS drudgery on which we used to blame the failures of windows upgrades.
And then another upgrade?! No way!
Win 8.1 upgrade. No Problems.
Win 10 upgrade. No Problems.
THIS IS GREAT! Has Microsoft finally done it? A kernel and shell stable enough to upgrade over again and again, and an update process slick enough to keep things churning nicely? It was truly remarkable. I had never formed such a storied relationship with a single OS install. It had never really been an option before. Windows installations were fleeting, like silent children or fresh milk in the fridge.

How about another upgrade?! The Win 10 Anniversary edition?

Nope. Couldn’t upgrade.
Sadly, it returned an error:

Turns out, I’m using an ‘unsupported disk layout’ which, for some reason, Windows 10 had suddenly decided it can’t abide by any more. I gots’ to get with the program!

After a bit of research, I find that what this error is really complaining about, is that my OS disk is still running an MBR partition. Most discs aren’t MBR anymore, because MBR can’t support more than 2-ish TB partitions (as well as some other fancy new boot features we won’t go in to). But my OS drive had always been smaller, faster drives. I ran WD raptors and velociraptors until SSDs became cheap enough for us mortals to afford. And even then, space came at a premium. So I’d clone my OS from one small drive to the next, never breaching that 2tb barrier. And as such, my partition remained MBR.

Maybe it was time to hold off on upgrades for a while? I was pleased with how Win 10 was working. And I had successfully upgraded my work machine to the anniversary edition. Nothing was there that I really cared about.

Except wait. Halo Forge requires the anniversary update. Gears of War 4 requires the anniversary update.


I couldn’t just slip back into my old mode of telling the young OS’s to stay off my lawn. I had to keep moving.
Oh well! It’s been nearly a decade since my last reinstall. Time to take the leap!

So I do it. I wipe away a decades’ worth of progress because I have no choice.

Or did I?

Had I read a little more, I would have seen that there are now streamlined ways to convert your disk to GPT from MBR without losing the data. Sadly, it looks like I didn’t have to reformat after all! How foolish of me to not read more about the issue! My stubborn old experience told me I had to reformat to go from MBR->GPT, and I didn’t question it!
A bit more time on the googles and I could’ve preserved this weird romance I was having with my OS. I really wanted to keep on going– see how far the single install could take me! And now, sadly, I will never know.

Rest in peace, sweet prince. For your pre-mature death, I blame myself. You deserved better– the decade-old OS install.

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